DE3619136A1 - Herstellung gegebenenfalls substituierter 6,8-dioxabicyclo (3.2.1) octane - Google Patents
Herstellung gegebenenfalls substituierter 6,8-dioxabicyclo (3.2.1) octaneInfo
- Publication number
- DE3619136A1 DE3619136A1 DE19863619136 DE3619136A DE3619136A1 DE 3619136 A1 DE3619136 A1 DE 3619136A1 DE 19863619136 DE19863619136 DE 19863619136 DE 3619136 A DE3619136 A DE 3619136A DE 3619136 A1 DE3619136 A1 DE 3619136A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- dioxabicyclo
- carbon atoms
- alcohol
- pyran
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- DYXJGWLSYLPWMO-UHFFFAOYSA-N 6,8-dioxabicyclo[3.2.1]octane Chemical class C1CCC2COC1O2 DYXJGWLSYLPWMO-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 18
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical class C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 8
- 230000009467 reduction Effects 0.000 claims abstract description 8
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003333 secondary alcohols Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000005292 vacuum distillation Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000004821 distillation Methods 0.000 abstract description 9
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract description 3
- -1 aluminium alkoxide Chemical class 0.000 abstract description 3
- 239000004411 aluminium Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 4
- YFRSJJSTFZPUSX-UHFFFAOYSA-N 1,4,5,7-tetramethyl-6,8-dioxabicyclo[3.2.1]octane Chemical compound O1C2(C)C(C)OC1(C)C(C)CC2 YFRSJJSTFZPUSX-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 3
- WBJNIPXRTMFVGW-UHFFFAOYSA-N 1-(2,5,6-trimethyl-3,4-dihydropyran-2-yl)ethanone Chemical compound CC(=O)C1(C)CCC(C)=C(C)O1 WBJNIPXRTMFVGW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SAVIBXWNETZRPQ-UHFFFAOYSA-N 1-(6-ethyl-2,5-dimethyl-3,4-dihydropyran-2-yl)propan-1-one Chemical compound CCC(=O)C1(C)CCC(C)=C(CC)O1 SAVIBXWNETZRPQ-UHFFFAOYSA-N 0.000 description 1
- QIYRGBNUCNZLNY-UHFFFAOYSA-N 1-(6-methyl-3,4-dihydro-2h-pyran-2-yl)ethanone Chemical compound CC(=O)C1CCC=C(C)O1 QIYRGBNUCNZLNY-UHFFFAOYSA-N 0.000 description 1
- XHEJCEGYLSAGOT-UHFFFAOYSA-N 2-(3,4-dihydro-2h-pyran-2-yl)ethanol Chemical class OCCC1CCC=CO1 XHEJCEGYLSAGOT-UHFFFAOYSA-N 0.000 description 1
- CLAIPNXKTFLQJJ-UHFFFAOYSA-N 5,7-diethyl-1,4-dimethyl-6,8-dioxabicyclo[3.2.1]octane Chemical compound O1C2(C)C(CC)OC1(CC)C(C)CC2 CLAIPNXKTFLQJJ-UHFFFAOYSA-N 0.000 description 1
- LYVSKAUJEKUBNH-UHFFFAOYSA-N 5,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane Chemical compound C1CCC2C(C)OC1(C)O2 LYVSKAUJEKUBNH-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012042 active reagent Substances 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 229940024546 aluminum hydroxide gel Drugs 0.000 description 1
- SMYKVLBUSSNXMV-UHFFFAOYSA-K aluminum;trihydroxide;hydrate Chemical compound O.[OH-].[OH-].[OH-].[Al+3] SMYKVLBUSSNXMV-UHFFFAOYSA-K 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863619136 DE3619136A1 (de) | 1986-06-06 | 1986-06-06 | Herstellung gegebenenfalls substituierter 6,8-dioxabicyclo (3.2.1) octane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863619136 DE3619136A1 (de) | 1986-06-06 | 1986-06-06 | Herstellung gegebenenfalls substituierter 6,8-dioxabicyclo (3.2.1) octane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3619136A1 true DE3619136A1 (de) | 1987-12-10 |
| DE3619136C2 DE3619136C2 (enExample) | 1989-03-02 |
Family
ID=6302470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863619136 Granted DE3619136A1 (de) | 1986-06-06 | 1986-06-06 | Herstellung gegebenenfalls substituierter 6,8-dioxabicyclo (3.2.1) octane |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3619136A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7820616B1 (en) | 2009-06-09 | 2010-10-26 | International Flavors & Fragrances, Inc. | Cyclic acetal compounds and their use in perfume compositions |
-
1986
- 1986-06-06 DE DE19863619136 patent/DE3619136A1/de active Granted
Non-Patent Citations (3)
| Title |
|---|
| Bull. Soc. Chim. France, 1969, S.956-962 * |
| Heterocycles 6, 1977, S.51-76 * |
| Recl. Trav. Chim. Pays Bas 98, 1979, S.346-352 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3619136C2 (enExample) | 1989-03-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69215070T2 (de) | Verfahren zur herstellung von 3-dpa-lacton | |
| DE2418715C2 (de) | Allensäureester | |
| DE1958600A1 (de) | Neue Isoxazolderivate und deren Herstellung | |
| EP0107806B1 (de) | Verfahren zur Herstellung von optisch aktiven Hydrochinonderivaten sowie von d-alpha-Tocopherol | |
| DE2319017C3 (de) | Verfahren zur Herstellung von Prostaglandinen der Eins-Reihe | |
| DE3619136C2 (enExample) | ||
| DE2511410A1 (de) | Ketolactone und verfahren zu ihrer herstellung | |
| DE69301120T2 (de) | Verfahren zur Herstellung von Vitamin-A-Säure | |
| DE2502919C2 (de) | Cyclopentan-Derivate, Verfahren zu ihrer Herstellung, sowie diese enthaltende pharmazeutische Zusammensetzungen | |
| DE3046106A1 (de) | Optisch reine bicyclo(2.2.2)oct-5-en-2.one, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2759994C2 (de) | Ketale von 4-(1-Hydroxy-1-methylethyl)-3-cyclohexen-1-on und Verfahren zu ihrer Herstellung | |
| DE2044698B2 (de) | Verfahren zur herstellung von cyclopentanderivaten mit der struktur der prostaglandine | |
| DE2601646C2 (enExample) | ||
| DE2848095A1 (de) | Substituierte perhydro-naphtofurane | |
| DE2415765C2 (enExample) | ||
| EP0112502A2 (de) | Omega,omega-Diacyloxy-2,6-dimethyl-octatriensäureester und -aldehyde, Verfahren zu ihrer Herstellung und Verwendung zur Synthese von Terpenverbindungen | |
| CH635305A5 (de) | 3-alkoxy- bzw. cycloalkoxy-4-homoisotwistan, verfahren zu seiner herstellung, riech- und geschmackstoffkomposition dasselbe enthaltend. | |
| EP0070566A1 (de) | C-8-substituierte 1,5-Dimethyl-bicyclo (3.2.1)octan-8-ole | |
| DE2246867A1 (de) | Tetrahydroxy-bicyclo- eckige klammer auf 3.3.0 eckige klammer zu -octane | |
| DE3602253A1 (de) | Verfahren zur herstellung von 4-monoacetalen des 2-methyl-2-buten-1,4-dials | |
| DE956682C (de) | Verfahren zur Herstellung des 8-[2, 6, 6-Trimethylcyclohexen- (1)-yl]-2, 6-dimethylokatrien-(2, 4, 6)-aldehyds-(1) | |
| DE3536956A1 (de) | Pyranderivate und ein verfahren zu ihrer herstellung | |
| DE1288612B (de) | Verfahren zur Herstellung von substituierten Tetrahydrofuranen bzw. Tetrahydropyranen | |
| DE69202169T2 (de) | Verfahren zur Herstellung von Irone. | |
| DE1620705C3 (de) | Verfahren zur Herstellung von substituierten 2-Alkoxy-carbonylmethyl-1,4,6,7-tetrahydro-11bH-benzo-(a)chinolizinen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: RWE-DEA AG FUER MINERALOEL UND CHEMIE, 2000 HAMBUR |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SASOL GERMANY GMBH, 22297 HAMBURG, DE |
|
| 8339 | Ceased/non-payment of the annual fee |